[2-[[3-(3-Dodecanoyloxytetradecanoylamino)-6-(hydroxymethyl)-5-phosphonooxy-4-(3-tetradecanoyloxytetradecanoyloxy)oxan-2-yl]oxymethyl]-3-hydroxy-5-(3-hydroxytetradecanoylamino)-6-phosphonooxyoxan-4-yl] 3-hydroxytetradecanoate

Base Information

• Chemical Name: [2-[[3-(3-Dodecanoyloxytetradecanoylamino)-6-(hydroxymethyl)-5-phosphonooxy-4-(3-tetradecanoyloxytetradecanoyloxy)oxan-2-yl]oxymethyl]-3-hydroxy-5-(3-hydroxytetradecanoylamino)-6-phosphonooxyoxan-4-yl] 3-hydroxytetradecanoate
• CAS No.: 95991-05-2
• Molecular Formula: C₉₄H₁₇₈N₂O₂₅P₂
• Molecular Weight: 1798.39
• DSSTox Substance ID: DTXSID50407727
• Mol file: 95991-05-2.mol

Synonyms:95991-05-2;Lipid A, diphosphoryl from Escherichia coli F583 (Rd mutant);[2-[[3-(3-dodecanoyloxytetradecanoylamino)-6-(hydroxymethyl)-5-phosphonooxy-4-(3-tetradecanoyloxytetradecanoyloxy)oxan-2-yl]oxymethyl]-3-hydroxy-5-(3-hydroxytetradecanoylamino)-6-phosphonooxyoxan-4-yl] 3-hydroxytetradecanoate;Lipid A, diphosphoryl from Salmonella enterica serotype minnesota Re 595 (Re mutant);DTXSID50407727

Chemical Property of [2-[[3-(3-Dodecanoyloxytetradecanoylamino)-6-(hydroxymethyl)-5-phosphonooxy-4-(3-tetradecanoyloxytetradecanoyloxy)oxan-2-yl]oxymethyl]-3-hydroxy-5-(3-hydroxytetradecanoylamino)-6-phosphonooxyoxan-4-yl] 3-hydroxytetradecanoate

Chemical Property:

• Appearance/Colour: White to tan powder
• PKA: 1.73±0.10(Predicted)
• Density: 1.13±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• XLogP3: 26.4
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 25
• Rotatable Bond Count: 88
• Exact Mass: 1798.22274800
• Heavy Atom Count: 123
• Complexity: 2710

Purity/Quality:

99% ^*data from raw suppliers

Lipid A, diphosphoryl from Salmonella enterica serotype minnesota Re 595 (Re mutant) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(C(OC(C1OP(=O)(O)O)CO)OCC2C(C(C(C(O2)OP(=O)(O)O)NC(=O)CC(CCCCCCCCCCC)O)OC(=O)CC(CCCCCCCCCCC)O)O)NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC
• Uses: Lipid A, diphosphoryl from?Escherichia coli?F583 (Rd mutant) has been used:to study the effect of various lipid A molecules on lung pericyte proliferation in vitroto test on THP-1 and J774A.1 cells for neopterin and nitrite formation respectivelyas lipopolysaccharides (LPS) derivatives in binding experimentsto stimulate the spleen cells and as a mitogen stimulation for toll like receptor 4 (TLR4)

Technology Process of [2-[[3-(3-Dodecanoyloxytetradecanoylamino)-6-(hydroxymethyl)-5-phosphonooxy-4-(3-tetradecanoyloxytetradecanoyloxy)oxan-2-yl]oxymethyl]-3-hydroxy-5-(3-hydroxytetradecanoylamino)-6-phosphonooxyoxan-4-yl] 3-hydroxytetradecanoate

There total 5 articles about [2-[[3-(3-Dodecanoyloxytetradecanoylamino)-6-(hydroxymethyl)-5-phosphonooxy-4-(3-tetradecanoyloxytetradecanoyloxy)oxan-2-yl]oxymethyl]-3-hydroxy-5-(3-hydroxytetradecanoylamino)-6-phosphonooxyoxan-4-yl] 3-hydroxytetradecanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

C144H220N2O25P2 (230966-96-8) → 2-deoxy-6-O-<2-deoxy-2-<(R)-3-dodecanoyloxytetradecanoylamino>-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranosyl>-3-O-<(R)-3-hydroxytetradecanoyl>-2-<(R)-3-hydroxytetradecanoylamino>-α-D-glucopyranose 1,4'-bis(phosphate) (95991-05-2,105307-37-7,130792-91-5) + 2-deoxy-6-O-<2-deoxy-2-<(R)-3-dodecanoyloxytetradecanoylamino>-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranosyl>-3-O-<(R)-3-hydroxytetradecanoyl>-2-<(R)-3-hydroxytetradecanoylamino>-D-glucose 4'-phosphate (88598-53-2,114420-33-6,103426-88-6)

Guidance literature:

With hydrogen; palladium; In tetrahydrofuran; at 20 ℃; under 5148.56 Torr;

DOI:10.1246/bcsj.72.1377

Reference yield: 75.0%

C139H212F6N2O25P2 → 2-deoxy-6-O-<2-deoxy-2-<(R)-3-dodecanoyloxytetradecanoylamino>-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranosyl>-3-O-<(R)-3-hydroxytetradecanoyl>-2-<(R)-3-hydroxytetradecanoylamino>-α-D-glucopyranose 1,4'-bis(phosphate) (95991-05-2,105307-37-7,130792-91-5)

Guidance literature:

With hydrogen; palladium; In tetrahydrofuran;

DOI:10.1055/s-2001-18109

Reference yield:

phenol-chloroform-petroleum ether extracted Escherichia coli F515 lipopolysaccharides → 2-deoxy-6-O-<2-deoxy-2-<(R)-3-dodecanoyloxytetradecanoylamino>-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranosyl>-3-O-<(R)-3-hydroxytetradecanoyl>-2-<(R)-3-hydroxytetradecanoylamino>-α-D-glucopyranose 1,4'-bis(phosphate) (95991-05-2,105307-37-7,130792-91-5)

Guidance literature:

With acetic acid; at 100 ℃; for 1h; pH=4.4;

DOI:10.1016/S0009-3084(03)00055-0

upstream raw materials:

C₁₄₂H₂₁₈N₂O₂₆P₂

C₁₄₄H₂₂₀N₂O₂₅P₂

Refernces

• 1、 Fukase,Zhang,Iseki,Oikawa,Fukase,Kusumoto. "New efficient route for synthesis of lipid A by using affinity separation". . p. 1693 - 1698. Retrieved 2007/10/03.
• 2、 Imoto, Masahiro,Yoshimura, Hiroyuki,Shimamoto, Tetsuo,Sakaguchi, Nobuki,Kusumoto, Shoichi,Shiba, Tetsuo. "Total Synthesis of Escherichia coli Lipid A, the Endotoxically Active Principle of Cell-Surface Lipopolysaccharide". . p. 2205 - 2214. Retrieved 2007/10/02.